Next Article in Journal
Synthesis and Biological Evaluation of 3-Benzisoxazolyl-4-indolylmaleimides as Potent, Selective Inhibitors of Glycogen Synthase Kinase-3β
Previous Article in Journal
Enantioselective Esterification of Ibuprofen under Microwave Irradiation
Molecules 2013, 18(5), 5482-5497; doi:10.3390/molecules18055482

Synthesis, Antifungal and Antitumor Activity of Novel (Z)-5-Hetarylmethylidene-1,3-thiazol-4-ones and (Z)-5-Ethylidene-1,3-thiazol-4-ones

1, 1, 2, 1, 1, 1, 3, 3, 2, 2 and 1,*
1 Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, A.A. 25360, Cali, Colombia 2 Pharmacognosy, Faculty of Biochemical and Pharmaceutical Sciences, Universidad Nacional de Rosario, Suipacha 531, (2000), Rosario, Argentina 3 Department of Inorganic and Organic Chemistry, Universidad de Jaén, 23071, Jaén, Spain
* Author to whom correspondence should be addressed.
Received: 8 April 2013 / Revised: 2 May 2013 / Accepted: 8 May 2013 / Published: 13 May 2013
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [289 KB, uploaded 18 June 2014]   |   Browse Figures


New hetaryl- and alkylidenerhodanine derivatives 3ad, 3e, and 4ad were prepared from heterocyclic aldehydes 1ad or acetaldehyde 1e. The treatment of several rhodanine derivatives 3ad and 3e with piperidine or morpholine in THF under reflux, afforded (Z)-5-(hetarylmethylidene)-2-(piperidin-1-yl)thiazol-4(5H)-ones and 2-morpholinothiazol-4(5H)-ones 5ad, 6ad, and (Z)-5-ethylidene-2-morpholinothiazol-4(5H)-one (5e), respectively, in good yields. Structures of all compounds were determined by IR, 1D and 2D NMR and mass spectrometry. Several of these compounds were screened by the U.S. National Cancer Institute (NCI) to assess their antitumor activity against 60 different human tumor cell lines. Compound 3c showed high activity against HOP-92 (Non-Small Cell Lung Cancer), which was the most sensitive cell line, with GI50 = 0.62 μM and LC50 > 100 μM from the in vitro assays. In vitro antifungal activity of these compounds was also determined against 10 fungal strains. Compound 3e showed activity against all fungal strains tested, but showed high activity against Saccharomyces cerevisiae (MIC 3.9 μg/mL).
Keywords: antifungal activity; antitumor activity; hetarylmethylidenerhodanine derivatives; piperidine; morpholine antifungal activity; antitumor activity; hetarylmethylidenerhodanine derivatives; piperidine; morpholine
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
MDPI and ACS Style

Insuasty, A.; Ramírez, J.; Raimondi, M.; Echeverry, C.; Quiroga, J.; Abonia, R.; Nogueras, M.; Cobo, J.; Rodríguez, M.V.; Zacchino, S.A.; Insuasty, B. Synthesis, Antifungal and Antitumor Activity of Novel (Z)-5-Hetarylmethylidene-1,3-thiazol-4-ones and (Z)-5-Ethylidene-1,3-thiazol-4-ones. Molecules 2013, 18, 5482-5497.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here


[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert